Water → HCID 86673516, compound

HRID 629035Notes

Reaction equation

HRID 629035 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1.[N:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCOCC1>[Cl:1][C:2]1[N:7]=[C:6]([C:14]2[CH:15]=[CH:16][N:11]=[CH:12][CH:13]=2)[C:5]([O:9][CH3:10])=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6014012,4-Dichloro-5-methoxypyrimidineHCID 2734379(Pyridin-4-yl)boronic acidHCID 22031701Potassium phosphate, tribasic, monohydrate

Product 1

HCID 86673516HCID 86673516, compoundYield 49.3%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2,4-dichloro-5-methoxy-pyrimidine (3.0 g, 1.0 eq.), 4-pyridinylboronic acid (2.26 g, 1.1 eq.), Pd(PPh3)2Cl2 (0.58 g, 0.05 eq.), K3PO4—H2O (10.67 g, 3.0 eq.), H2O (3 ml) and 1,4-Dioxane (20.0 ml) was heated at 90° C. and refluxed overnight. The solvent was removed in vacuo, and the residue was extracted with EA and water. The combined organic layers was wash with brine, dried and evaporated in vacuo. The crude was purified by chromatography to give a yellow thick liquid (1.83 g, 49.26%).

Workup

  1. temperaturerefluxed overnight
  2. customThe solvent was removed in vacuo
  3. extractionthe residue was extracted with EA and water
  4. washThe combined organic layers was wash with brine
  5. customdried
  6. customevaporated in vacuo
  7. customThe crude was purified by chromatography

Sources & evidence

ORD record
ord-7fe947185d7644e194c59e244a69c5b8
Source dataset
uspto-grants-2016_04
Patent number
US09315491B2

Reaction notes

Loading…